Synthesis of a novel building block for the preparation of multi-chromophoric sensitizers for panchromatic dye-sensitized solar cells

Watson, Brian L.; Moore, Thomas A.; Moore, Ana L.; Gust, Devens

doi:10.1016/j.dyepig.2016.09.037

Cited by 17 publications

(4 citation statements)

References 26 publications

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“…The excited state would ideally have a long lifetime to effectively drive subsequent processes such as energy/electron transfer that initiate chemistry or photocurrent. Although there have been various approaches to attaining molecular panchromatic absorbers, − no clear design criteria have emerged to attain superchromophores that simultaneously afford panchromatic absorption and favorable excited-state properties.…”

Section: Introductionmentioning

confidence: 99%

Origin of Panchromaticity in Multichromophore–Tetrapyrrole Arrays

et al. 2018

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Panchromatic absorbers that have robust photophysical properties enable new designs for molecular-based light-harvesting systems. Herein, we report experimental and theoretical studies of the spectral, redox, and excited-state properties of a series of perylene-monoimide-ethyne-porphyrin arrays wherein the number of perylene-monoimide units is stepped from one to four. In the arrays, a profound shift of absorption intensity from the strong violet-blue (B and B) bands of typical porphyrins into the green, red, and near-infrared (Q and Q) regions stems from mixing of chromophore and tetrapyrrole molecular orbitals (MOs), which gives multiplets of MOs having electron density spread over the entire array. This reduces the extensive mixing between porphyrin excited-state configurations and the transition-dipole addition and subtraction that normally leads to intense B and weak Q bands. Reduced configurational mixing derives from moderate effects of the ethyne and perylene on the MO energies and a more substantial effect of electron-density delocalization to reduce the configuration-interaction energy. Quantitative oscillator-strength analysis shows that porphyrin intensity is also shifted into the perylene-like green-region absorption and that the ethyne linkers lend absorption intensity. The reduced porphyrin configurational mixing also endows the S state with bacteriochlorin-like properties, including a 1-5 ns lifetime.

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Section: Introductionmentioning

confidence: 99%

Origin of Panchromaticity in Multichromophore–Tetrapyrrole Arrays

et al. 2018

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“…Globally, the BF 2 -carrying molecules are the most popular organic fluorophores to date and, as Ziessel pointed out, they constitute an “El Dorado for fluorescence tools” . Some BODIPYs exhibit near-infrared (NIR) fluorescence in solution − but also as a film on surfaces, so that several have been used as red photon harvesters in solar cells. − However, the fluorescence quantum yields remain rather small for the most red-shifted emitters. To lift this limitation, it is important to understand the key parameters controlling the emission properties so to allow the rational and systematic tuning of the spectroscopic features, further paving the way toward applications of these dyes in several fields, e.g., bioimaging ,, and sensing. − …”

Section: Introductionmentioning

confidence: 99%

Photophysical Properties of Phenacylphenantridine Difluoroboranyls: Effect of Substituent and Double Benzannulation

et al. 2017

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In this study we present a new series of phenantridine-based substituted difluoroboranyls. The effects of substitution and double benzannulation on their photophysical properties were examined with experimental techniques and compared with the results obtained for previously reported quinoline and isoquinoline derivatives. The experimental characterizations are supported by state-of-the-art quantum-chemical calculations. In particular, the theoretical calculations were performed to gain insights into the complex nature of the relevant excited-states. These calculations reveal that both the nature of the substituent and its position on the phenyl ring significantly impact the magnitude of the electronic charge transferred upon excitation. Additionally, vibrationally resolved spectra were determined allowing for the analysis of the key vibrations playing a role in the band shapes.

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“…Porphyrins are some of the most remarkable sensitizers in dye-sensitized solar cells (DSSCs), achieving some of the highest power conversion efficiencies (PCEs) to date [1][2][3]. Multi-chromophoric porphyrin dyes having more than one chromophore, either increasing the extinction coefficient or extending the photon absorption wavelength range as an alternative to the co-sensitization approach, have attracted the interest of researchers to further increase the DSSC performance [4][5][6][7][8][9][10][11]. One of the interesting aspects of the multi-chromophoric design is that the electronic communication between the chromophores can be inhibited by a twisted threedimensional structure, weakening the dispersion forces (polarizability of the molecule) and elongating the electron lifetime [9].…”

Section: Introductionmentioning

confidence: 99%

Effect of the second chromophore energy gap on photo-induced electron injection in di-chromophoric porphyrin-sensitized solar cells

Zhao

2018

R. Soc. open sci.

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This work investigates the effect of the second chromophore energy gap on charge generation in porphyrin-based di-chromophoric dye-sensitized solar cells (DSSCs). Three di-chromophoric porphyrin dyes (PorY, PorO and PorR) containing three organic chromophores with decreasing frontier orbital energy offsets, including a carbazole-triphenylamine chromophore (yellow, Y), a carbazole fused-thiophene chromophore (orange, O) or a carbazole-thiophene benzothiadiazole thiophene chromophore (red, R), were investigated using optical and electrochemical methods, steady-state photoluminescence and photovoltaic device characterization. Energy transfer from the organic chromophore to the porphyrin was suggested in PorY and PorO as the main charge generation mechanism in DSSCs using these di-chromophoric dyes. On the other hand, electron transfer from the photo-excited porphyrin to the organic chromophore as a competing pathway leading to the loss of photocurrent is suggested for PorR-sensitized solar cells. The latter pathway leading to a loss of photocurrent is due to the lower lying lowest unoccupied molecular orbital of the additional organic chromophore (R) and suggests the limitation of the current di-chromophoric approach to increase the overall efficiency of DSSCs.

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Synthesis of a novel building block for the preparation of multi-chromophoric sensitizers for panchromatic dye-sensitized solar cells

Cited by 17 publications

References 26 publications

Origin of Panchromaticity in Multichromophore–Tetrapyrrole Arrays

Origin of Panchromaticity in Multichromophore–Tetrapyrrole Arrays

Photophysical Properties of Phenacylphenantridine Difluoroboranyls: Effect of Substituent and Double Benzannulation

Effect of the second chromophore energy gap on photo-induced electron injection in di-chromophoric porphyrin-sensitized solar cells

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